CH179690A - Process for the preparation of 1,3-dimethyl-5,5-phenylmethylhydantoin. - Google Patents

Process for the preparation of 1,3-dimethyl-5,5-phenylmethylhydantoin.

Info

Publication number
CH179690A
CH179690A CH179690DA CH179690A CH 179690 A CH179690 A CH 179690A CH 179690D A CH179690D A CH 179690DA CH 179690 A CH179690 A CH 179690A
Authority
CH
Switzerland
Prior art keywords
phenylmethylhydantoin
dimethyl
preparation
alcohol
methyl
Prior art date
Application number
Other languages
German (de)
Inventor
Sandoz Chemische Fabri Vormals
Original Assignee
Chem Fab Vormals Sandoz
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chem Fab Vormals Sandoz filed Critical Chem Fab Vormals Sandoz
Publication of CH179690A publication Critical patent/CH179690A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  \'erfahren zur Darstellung von     1,3-Dimethyl-5,5-phenylmethylhydantoin.       Das vorliegende Verfahren betrifft die  Darstellung von     1,3-Dimethyl-5,5-phenyl-          rnethylhy        dantoin    und ist dadurch gekenn  zeichnet, dass man     3-Methyl-5,5-phenyl-          niethylhydantoin    mit     Dimethylstilfat        behan-          rlelt.     



  <I>Beispiel:</I>  <I>20,4</I>     gr        3-3lethyl-5,5-phenylmethylhy        dan-          toin    werden in 180     ein-    Alkohol gelöst und  mit     12,(l        cm3    Natronlauge     (4070    versetz  und bei 70   unter     Turbinieren    tropfenweise  <B>15,1</B>     gr        Dimethylsulfat    zugegeben. Man  rührt eine Stunde weiter, destilliert den  grössten Teil des Alkohols ab und nimmt  mit     Wasser    auf.

   Das anfangs ölig sich aus  scheidende Reaktionsprodukt erstarrt bald  und wird aus     verd.    Alkohol     umkristallisiert:z     Das     1,3-Dimethyl-5,5-phenylmethylhydan-          toin    kristallisiert in farblosen, feinen Plätt  chen,     Smp.    75 bis 77  , ist leicht     löslieh    in  Alkohol, Essigester, Chloroform, Benzol,  mässig in     Ligroin    und     Petroläther.    unlöslich  in     Wasser,    ebenso in Alkali.  



  0,3344     gr    verbrauchen nach     Kjeldahl     31,14 cm' n/10     2S0,       für     C"H"02N2    berechnet     12,84%    N  gefunden 13,05 % N  Zu derselben Verbindung gelangt man  auch ausgehend vom     5,5-Phenylmethylhyd-          antoin,    wenn mit doppelter Menge Natron  lauge und     Methylsulfat,    in wässeriger oder  alkoholischer Lösung gearbeitet wird.



  Learn about the preparation of 1,3-dimethyl-5,5-phenylmethylhydantoin. The present process relates to the preparation of 1,3-dimethyl-5,5-phenyl-methylhydantoin and is characterized in that 3-methyl-5,5-phenyl-diethylhydantoin is treated with dimethylstilfate.



  <I> Example: </I> <I> 20.4 </I> gr 3-3lethyl-5,5-phenylmethylhydantoin are dissolved in 180% alcohol and mixed with 12.1 cm3 sodium hydroxide solution (4070 and <B> 15.1 </B> g of dimethyl sulfate are added dropwise with turbines at 70. The mixture is stirred for a further hour, most of the alcohol is distilled off and taken up in water.

   The initially oily reaction product soon solidifies and is recrystallized from dilute alcohol: the 1,3-dimethyl-5,5-phenylmethylhydantoin crystallizes in colorless, fine platelets, m.p. Alcohol, ethyl acetate, chloroform, benzene, moderate in ligroin and petroleum ether. insoluble in water, also in alkali.



  According to Kjeldahl, 0.3344 gr use 31.14 cm 'n / 10 2S0, for C "H" 02N2 calculated 12.84% N found 13.05% N The same compound is also obtained starting from 5,5-phenylmethylhydantoin when working with twice the amount of sodium hydroxide and methyl sulfate in an aqueous or alcoholic solution.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 1,3-Di- fuethyl-5,5-phenylmethylhydantoin, dadurch gekennzeichnet, dass man 3-Methyl-5,5-phe- nylmethylhydantoin mit Dimethylsulfat be handelt. Das bis jetzt unbekannte 1,3-Dimethyl- 5,5-phenylmethy lhyda.ntoin kristallisiert in farblosen, feinen Plättchen von Smp. 75 bis 7 7 C und besitzt die Formel EMI0001.0049 Es soll in der Therapie Verwendung finden. PATENT CLAIM: Process for the preparation of 1,3-di-fuethyl-5,5-phenylmethylhydantoin, characterized in that 3-methyl-5,5-phenylmethylhydantoin is treated with dimethyl sulfate. The hitherto unknown 1,3-dimethyl-5,5-phenylmethy lhyda.ntoin crystallizes in colorless, fine platelets with a melting point of 75 to 7 ° C. and has the formula EMI0001.0049 It should be used in therapy.
CH179690D 1934-06-06 1934-06-06 Process for the preparation of 1,3-dimethyl-5,5-phenylmethylhydantoin. CH179690A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH179690T 1934-06-06
CH166004T 1934-06-06

Publications (1)

Publication Number Publication Date
CH179690A true CH179690A (en) 1935-09-15

Family

ID=25718217

Family Applications (1)

Application Number Title Priority Date Filing Date
CH179690D CH179690A (en) 1934-06-06 1934-06-06 Process for the preparation of 1,3-dimethyl-5,5-phenylmethylhydantoin.

Country Status (1)

Country Link
CH (1) CH179690A (en)

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